In this paper, in order to find novel biologically active pyrazole oximes, a series of pyrazole oxime compounds bearing a substituted pyridyl unit were prepared. Bioassays showed that some target compounds were found to have good acaricidal activity against Tetranychus cinnabarinus at a concentration of 500 μg/mL, compound 9q especially displayed potent acaricidal activity against T. cinnabarinus when the concentration was reduced to 100 μg/mL. Interestingly, most target compounds possessed excellent insecticidal activities against Oriental armyworm at 500 μg/mL. Moreover, some compounds were active against Aphis medicaginis and Nilaparvata lugens at 500 μg/mL. Additionally, compounds 9b, 9g, 9l, 9p, 9q, 9r, 9s, 9t, 9u, and 9v displayed significant antiproliferative activities against HepG2 cells with IC50 values of 1.53–17.27 μM, better than that of the control 5-fluorouracil (IC50 = 35.67 μM).